WO2017006888A1 - Composition de résine, pré-imprégné ou feuille de résine mettant en œuvre cette composition, plaque stratifiée mettant en œuvre ceux-ci, et carte de circuit imprimé - Google Patents

Composition de résine, pré-imprégné ou feuille de résine mettant en œuvre cette composition, plaque stratifiée mettant en œuvre ceux-ci, et carte de circuit imprimé Download PDF

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Publication number
WO2017006888A1
WO2017006888A1 PCT/JP2016/069739 JP2016069739W WO2017006888A1 WO 2017006888 A1 WO2017006888 A1 WO 2017006888A1 JP 2016069739 W JP2016069739 W JP 2016069739W WO 2017006888 A1 WO2017006888 A1 WO 2017006888A1
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WO
WIPO (PCT)
Prior art keywords
group
resin composition
mass
formula
resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2016/069739
Other languages
English (en)
Japanese (ja)
Inventor
与一 高野
展義 大西
克哉 富澤
直樹 鹿島
博史 高橋
英祐 志賀
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Priority to JP2017527438A priority Critical patent/JP6774032B2/ja
Priority to US15/738,400 priority patent/US10703874B2/en
Priority to EP16821357.7A priority patent/EP3321289B1/fr
Priority to KR1020177033056A priority patent/KR102605760B1/ko
Priority to CN201680039769.1A priority patent/CN107735409B/zh
Publication of WO2017006888A1 publication Critical patent/WO2017006888A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors
    • C08G73/125—Unsaturated polyimide precursors the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen in the main chain
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/02—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments
    • B32B17/04—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments bonded with or embedded in a plastic substance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
    • B32B5/28—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer impregnated with or embedded in a plastic substance
    • C—CHEMISTRY; METALLURGY
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • C08F222/402—Alkyl substituted imides
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F222/40—Imides, e.g. cyclic imides
    • C08F222/404—Imides, e.g. cyclic imides substituted imides comprising oxygen other than the carboxy oxygen
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F222/40—Imides, e.g. cyclic imides
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    • C08F236/20—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds unconjugated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
    • C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W42/00—Arrangements for protection of devices
    • H10W42/121—Arrangements for protection of devices protecting against mechanical damage
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W70/00—Package substrates; Interposers; Redistribution layers [RDL]
    • H10W70/60—Insulating or insulated package substrates; Interposers; Redistribution layers
    • H10W70/67—Insulating or insulated package substrates; Interposers; Redistribution layers characterised by their insulating layers or insulating parts
    • H10W70/69—Insulating materials thereof
    • H10W70/695—Organic materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/02—Composition of the impregnated, bonded or embedded layer
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    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
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    • B32B2457/00—Electrical equipment
    • B32B2457/08—PCBs, i.e. printed circuit boards
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    • C08J2333/24—Homopolymers or copolymers of amides or imides
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    • H—ELECTRICITY
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    • H10W70/00—Package substrates; Interposers; Redistribution layers [RDL]
    • H10W70/01—Manufacture or treatment
    • H10W70/05—Manufacture or treatment of insulating or insulated package substrates, or of interposers, or of redistribution layers

Definitions

  • the present invention relates to a resin composition, a prepreg or resin sheet using the resin composition, a laminate using the prepreg or resin sheet, and a printed wiring board using the resin composition.
  • One of the measures is to reduce the thermal expansion of the insulating layer used for the printed wiring board. This is a technique for suppressing warpage by bringing the thermal expansion coefficient of a printed wiring board close to the thermal expansion coefficient of a semiconductor element, and is currently being actively worked on (see, for example, Patent Documents 1 to 3).
  • methods for suppressing the warpage of the semiconductor plastic package include increasing the rigidity of the laminated board (higher rigidity) and increasing the glass transition temperature of the laminated board (high Tg). (For example, see Patent Documents 4 and 5).
  • JP 2013-216884 A Japanese Patent No. 3173332 JP 2009-035728 A JP 2013-001807 A JP2011-177892A
  • the technique of increasing the Tg of the laminated plate improves the elastic modulus during reflow, and thus is effective in reducing the warpage of the semiconductor plastic package.
  • the technique using high Tg causes deterioration in moisture absorption heat resistance due to an increase in crosslink density and voids due to deterioration in moldability. Therefore, it is practically used in the field of electronic materials that require extremely high reliability. Often problematic. Therefore, a method for solving these problems is desired.
  • an object of the present invention is to provide a resin composition having a good elastic modulus maintenance factor and a low coefficient of thermal expansion.
  • a resin composition comprising an alkenyl-substituted nadiimide (A), a maleimide compound (B), and an amino-modified silicone (C).
  • a resin composition according to [1] wherein at least a part of the maleimide compound (B) is included in the form of a prepolymer (P) polymerized with the amino-modified silicone (C).
  • each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • R 2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or The group represented by the general formula (2) or (3) is shown.
  • R 3 represents a substituent represented by a methylene group, an isopropylidene group, CO, O, S, or SO 2.
  • each R 4 independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.
  • the maleimide compound (B) is bis (4-maleimidophenyl) methane, 2,2-bis ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane, bis (3-ethyl-5-methyl-4-maleimidophenyl) Any one of [1] to [4], which is at least one selected from the group consisting of methane, polytetramethylene oxide-bis (4-maleimidobenzoate) and a maleimide compound represented by the following general formula (6) The resin composition described in 1.
  • R 5 each independently represents a hydrogen atom or a methyl group, and n 1 represents an integer of 1 or more.
  • R 5 each independently represents a hydrogen atom or a methyl group, and n 1 represents an integer of 1 or more.
  • each R 6 independently represents a hydrogen atom or a methyl group, and n 2 represents an integer of 1 or more.
  • R 7 each independently represents a hydrogen atom or a methyl group, and n 3 represents an integer of 1 or more.
  • X imidazole compound represented by the following general formula (I):
  • each Ar is independently a phenyl group, naphthalene group, biphenyl group, anthracene group or a hydroxyl group modified product thereof, and R is a hydrogen atom, an alkyl group or a hydroxyl group modified product thereof, or an aryl group.
  • the content of the inorganic filler (D) is 50 to 500 parts by mass with respect to a total of 100 parts by mass of the alkenyl-substituted nadiimide (A), maleimide compound (B), and amino-modified silicone (C).
  • a prepreg obtained by impregnating or coating a substrate with the resin composition according to any one of [1] to [13].
  • a metal foil-clad laminate comprising a cured product of a laminate in which at least one selected from the group consisting of the prepreg according to [14] and [15] and the resin sheet according to [16] and a metal foil are laminated.
  • a printed wiring board comprising an insulating layer and a conductor layer formed on the surface of the insulating layer, wherein the insulating layer comprises the resin composition according to any one of [1] to [13] Board.
  • the resin composition of this embodiment contains an alkenyl-substituted nadiimide (A), a maleimide compound (B), and an amino-modified silicone (C). Further, the resin composition of the present embodiment is improved in peel strength that at least a part of the maleimide compound (B) is included in the form of a prepolymer (P) polymerized with the amino-modified silicone (C). In view of the tendency to improve desmear resistance, improve moldability, or suppress bleeding out of the silicone component. Hereinafter, the resin composition will be described in detail.
  • alkenyl-substituted nadiimide (A) used in the present embodiment is not particularly limited as long as it is a compound having one or more alkenyl-substituted nadiimide groups in the molecule. Specific examples thereof include compounds represented by the following general formula (1).
  • each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • R 2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or the following general formula
  • the group represented by Formula (2) or (3) is shown.
  • R 3 represents a substituent represented by a methylene group, an isopropylidene group, CO, O, S, or SO 2 .
  • R 4 represents an independently selected alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.
  • alkenyl substituted nadiimide (A) represented by Formula (1) examples include, but are not limited to, compounds represented by the following formula (4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and compounds represented by the following formula (5). (BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.)). These may be used alone or in combination of two or more.
  • the content of the alkenyl-substituted nadiimide (A) is not particularly limited, and the number of alkenyl groups ( ⁇ ) and maleimide which are one of the functional groups of the alkenyl-substituted nadiimide (A) described later although it may be determined by the ratio of the number of functional groups to the number of maleimide groups ( ⁇ ) ([ ⁇ / ⁇ ]) of the compound, 10 to 60 parts by mass with respect to 100 parts by mass in total of components (A) to (C) It is preferably 15 to 50 parts by mass, more preferably 20 to 40 parts by mass.
  • the ratio ([ ⁇ / ⁇ ]) of the number of alkenyl groups ( ⁇ ) of the alkenyl-substituted nadiimide (A) and the number of maleimide groups ( ⁇ ) of the maleimide compound (B) is preferably 0.9 to 4.3. More preferably, it is 0.5 to 4.0, and more preferably 1.5 to 3.0.
  • the maleimide compound (B) used in the present embodiment is not particularly limited as long as it is a compound having one or more maleimide groups in the molecule. Specific examples thereof include, for example, N-phenylmaleimide, N-hydroxyphenylmaleimide, bis (4-maleimidophenyl) methane, 2,2-bis ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane, bis (3 , 5-dimethyl-4-maleimidophenyl) methane, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, bis (3,5-diethyl-4-maleimidophenyl) methane, polytetramethylene oxide-bis (4-maleimidobenzoate), maleimide compounds represented by the following formula (6), prepolymers of these maleimide compounds, or prepolymers of maleimide compounds and amine compounds. These may be used alone or in combination of two or more.
  • R 5 each independently represents a hydrogen atom or a methyl group, and among them, a hydrogen atom is preferable.
  • n 1 represents an integer of 1 or more.
  • the upper limit value of n 1 is preferably 10, more preferably 7.
  • the resin composition of the present embodiment includes a prepolymer (P) obtained by polymerizing a maleimide compound (B) and an amino-modified silicone (C), an alkenyl-substituted nadiimide (A), a maleimide compound (B), It is preferable to contain.
  • a maleimide compound (B) (hereinafter also referred to as “maleimide compound (B-1)”) used as a raw material for the prepolymer (P), and a maleimide contained in the resin composition separately from the maleimide compound (B-1)
  • the compound (B) (hereinafter also referred to as “maleimide compound (B-2)”) may be the same or different, but is preferably different.
  • maleimide compound (B-1) examples include bis (4-maleimidophenyl) methane, 2,2-bis ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane, and bis (3-ethyl-5-methyl-4- Maleimidophenyl) methane, polytetramethylene oxide-bis (4-maleimidobenzoate), maleimide compounds represented by the above general formula (6) are preferred, and 2,2-bis ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane Bis (3-ethyl-5-methyl-4-maleimidophenyl) methane is more preferred, and 2,2-bis ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane is more preferred.
  • maleimide compound (B-2) examples include bis (4-maleimidophenyl) methane, 2,2-bis ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane, bis (3-ethyl-5-methyl-4- Maleimidophenyl) methane, polytetramethylene oxide-bis (4-maleimidobenzoate), maleimide compounds represented by the above general formula (6) are preferred, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, Polytetramethylene oxide-bis (4-maleimidobenzoate) and a maleimide compound represented by the following general formula (6) are more preferred, and a maleimide compound represented by the above general formula (6) is more preferred.
  • Maleimide compounds (B-1) and (B-2) may be used alone or in combination of two or more.
  • the content of the maleimide compound (B) is not particularly limited, and the ratio between the number of alkenyl groups of the alkenyl-substituted nadiimide (A) and the number of maleimide groups of the maleimide compound (B) described above.
  • it is preferably 30 to 80 parts by weight, more preferably 35 to 70 parts by weight, more preferably 40 to 60 parts by weight based on 100 parts by weight of the total of components (A) to (C). It is more preferable to use a part by mass.
  • the content of the maleimide compound (B-1) is amino-modified silicone. It is determined by the number of amino groups in (C). That is, the ratio ([B-1 / C]) of the number of maleimide groups of the maleimide compound (B-1) to the number of amino groups of the amino-modified silicone (C) is preferably 1.0 to 20.0. More preferably, it is set to ⁇ 15.0, and more preferably 6.0 to 12.0.
  • the content of the maleimide compound (B-2) is preferably the difference between the content of the maleimide compound (B) and the content of the maleimide compound (B-1) ([(B- (B-1)]).
  • amino-modified silicone (C) used in the present embodiment is not particularly limited as long as it is a compound having one or more amino groups in the molecule. Specific examples thereof include compounds represented by the following general formula (Y).
  • each R 9 independently represents a hydrogen atom, a methyl group or a phenyl group, and among them, a methyl group is preferable.
  • R 10 each independently represents an alkylene group having 1 to 10 carbon atoms which may have a side chain, and among them, an alkylene group having 2 to 10 carbon atoms is preferable.
  • n represents an integer of 0 or more.
  • the amino group equivalent of the amino-modified silicone (C) is preferably from 130 to 6000, more preferably from 400 to 3000, and even more preferably from 600 to 2500. By using such an amino-modified silicone (C), it is possible to obtain a resin composition having a good elastic modulus retention rate and a lower thermal expansion coefficient.
  • the content of the amino-modified silicone (C) is not particularly limited, but is 1 to 40 parts by mass with respect to 100 parts by mass in total of the components (A) to (C).
  • the content is 3 to 30 parts by mass, more preferably 5 to 20 parts by mass.
  • the resin composition of the present embodiment other resins can be added in addition to the components (A) to (C) as long as desired characteristics are not impaired.
  • resin such as an epoxy resin, a benzoxazine compound, a phenol resin, and a thermoplastic resin, is mentioned.
  • resin such as an epoxy resin, a benzoxazine compound, a phenol resin, and a thermoplastic resin.
  • the epoxy resin is not particularly limited as long as it is a compound having two or more epoxy groups in one molecule.
  • bisphenol A type epoxy resin bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolak type epoxy resin, cresol novolac type epoxy resin, biphenyl type epoxy resin, naphthalene type epoxy resin, naphthylene ether type epoxy resin, trifunctional phenol Type epoxy resin, tetrafunctional phenol type epoxy resin, glycidyl ester type epoxy resin, phenol aralkyl type epoxy resin, biphenyl aralkyl type epoxy resin, biphenyl novolac type epoxy Fat, aralkyl novolak type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, a polyol type epoxy resin, isocyanurate ring-containing epoxy resin, or these halides and the like.
  • Epoxy resins may be used alone or in combination of two or more.
  • the content of the epoxy resin is not particularly limited, but is preferably 3 to 40 parts by mass, more preferably 3 to 30 parts by mass with respect to a total of 100 parts by mass of the components (A) to (C). More preferably, it is 3 to 20 parts by mass.
  • the content of the epoxy resin is within the above range, the heat resistance and curability tend to be further improved.
  • the resin composition of this embodiment further contains an inorganic filler (D).
  • the inorganic filler (D) used in the present embodiment is not particularly limited as long as it has insulating properties.
  • silica from the viewpoint of low thermal expansion
  • alumina or aluminum nitride from the viewpoint of high thermal conductivity
  • the content of the inorganic filler (D) is not particularly limited, but is 50 to 500 parts by mass with respect to 100 parts by mass in total of the components (A) to (C). From the viewpoint of characteristics such as low thermal expansion and high thermal conductivity, it is preferably 100 to 300 parts by mass, more preferably 100 to 250 parts by mass.
  • the resin composition of this embodiment preferably further contains a cyanate ester compound.
  • a cyanate ester compound for example, the naphthol aralkyl type cyanate ester represented by following General formula (7), the novolak type cyanic acid represented by following General formula (8) Ester, biphenylaralkyl cyanate ester, bis (3,3-dimethyl-4-cyanatophenyl) methane, bis (4-cyanatophenyl) methane, 1,3-dicyanatobenzene, 1,4-dicyanatobenzene 1,3,5-tricyanatobenzene, 1,3-dicyanatonaphthalene, 1,4-dicyanatonaphthalene, 1,6-dicyanatonaphthalene, 1,8-dicyanatonaphthalene, 2,6-dicyanatonaphthalene 2,7-dicyanatonaphthalene, 1,3,6-tricyanatonaphthal
  • the naphthol aralkyl cyanate ester compound represented by the following general formula (7), the novolac cyanate ester and the biphenyl aralkyl cyanate ester represented by the following general formula (8) are excellent in flame retardancy and cured. It is particularly preferable because of its high properties and a low thermal expansion coefficient of the cured product.
  • each R 6 independently represents a hydrogen atom or a methyl group, and among them, a hydrogen atom is preferable.
  • n 2 is an integer of 1 or more.
  • the upper limit value of n 2 is preferably 10, more preferably 6.
  • R 7 each independently represents a hydrogen atom or a methyl group, and among them, a hydrogen atom is preferable.
  • n 3 is an integer of 1 or more.
  • the upper limit value of n 3 is preferably 10, more preferably 7.
  • cyanate ester compounds are not particularly limited, and any existing method as a cyanate ester synthesis method may be used. Specifically, it can be obtained by reacting a naphthol aralkyl type phenol resin represented by the following general formula (9) with cyanogen halide in an inert organic solvent in the presence of a basic compound. Alternatively, a similar naphthol aralkyl type phenol resin and a salt of a basic compound may be formed in a solution containing water, and then a two-phase interface reaction with cyanogen halide may be performed for synthesis. it can.
  • each R 8 independently represents a hydrogen atom or a methyl group, and among them, a hydrogen atom is preferable.
  • n 4 represents an integer of 1 or more.
  • upper limit of n 4 is preferably 10, more preferably 6.
  • the naphthol aralkyl cyanate ester compounds include naphthols such as ⁇ -naphthol and ⁇ -naphthol, p-xylylene glycol, ⁇ , ⁇ '-dimethoxy-p-xylene, 1,4-di (2-hydroxy- It can be selected from those obtained by condensing naphthol aralkyl resin obtained by reaction with 2-propyl) benzene and cyanic acid.
  • the content of the cyanate ester compound is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass in total of the components (A) to (C). More preferably, it is more preferably 5 to 5 parts by mass, and still more preferably 0.3 to 3 parts by mass.
  • the resin composition of this embodiment further contains an imidazole compound (X) represented by the following general formula (I).
  • each Ar is independently a phenyl group, naphthalene group, biphenyl group, anthracene group or a hydroxyl group modified product thereof, and R is a hydrogen atom, an alkyl group or a hydroxyl group modified product thereof, or an aryl group.
  • the imidazole compound (X) represented by the general formula (I) used in the present embodiment has an effect of accelerating curing and has an effect of increasing the glass transition temperature of the cured product.
  • Examples of the imidazole substituent Ar include a phenyl group, a naphthalene group, a biphenyl group, an anthracene group, and a hydroxyl group-modified product thereof, among which a phenyl group is preferable.
  • the imidazole substituent R is preferably a hydrogen atom, an alkyl group or a hydroxyl-modified product thereof, and an aryl group such as a phenyl group, and more preferably a phenyl group for both the Ar group and the R group.
  • the imidazole compound (X) represented by the general formula (I) is particularly preferably 2,4,5-triphenylimidazole from the viewpoints of curing degree and glass transition temperature.
  • the content of the imidazole compound (X) represented by the general formula (I) is from the viewpoint of storage stability of the prepreg and moldability when processing into a copper-clad laminate.
  • the range of 0.1 to 10 parts by weight is preferable with respect to 100 parts by weight of the total resin composition, and the range of 0.2 to 5 parts by weight is particularly preferable.
  • the resin composition of this embodiment may contain silicone powder.
  • Silicone powder acts as a flame retardant aid that delays the burning time and enhances the flame retardant effect.
  • the silicone powder is not particularly limited.
  • the surface of the fine powder made by addition of vinyl group-containing dimethylpolysiloxane and methylhydrogenpolysiloxane was coated with polymethylsilsesquioxane in which the siloxane bonds were crosslinked in a three-dimensional network.
  • the average particle size (D50) of the silicone powder is not particularly limited, but the average particle size (D50) is preferably 1 to 15 ⁇ m in consideration of dispersibility.
  • the content of the silicone powder is not particularly limited, but is preferably 3 to 120 parts by mass with respect to 100 parts by mass in total of the components (A) to (C). In particular, 3 to 60 parts by mass is particularly preferable because the dispersibility may be lowered.
  • silane coupling agents and wetting and dispersing agents In the resin composition of this embodiment, in order to improve the dispersibility of the fine particles and the adhesive strength between the resin and the fine particles or the glass cloth, a silane coupling agent or a wetting and dispersing agent can be used in combination. These silane coupling agents are not particularly limited as long as they are silane coupling agents generally used for inorganic surface treatment.
  • aminosilanes such as ⁇ -aminopropyltriethoxysilane, N- ⁇ - (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, epoxysilanes such as ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -Acrylic silanes such as acryloxypropyltrimethoxysilane, cationic silanes such as N- ⁇ - (N-vinylbenzylaminoethyl) - ⁇ -aminopropyltrimethoxysilane hydrochloride, phenylsilanes, etc. It is also possible to use one kind or a combination of two or more kinds as appropriate.
  • the wetting and dispersing agent is not particularly limited as long as it is a dispersion stabilizer used for coatings.
  • wetting and dispersing agents such as DISPER-110, 111, 118, 180, 161, BYK-W996, W9010, W903 manufactured by Big Chemie Japan Co., Ltd. may be mentioned.
  • Oxides such as azobisnitrile; N, N-dimethylbenzylamine, N, N-dimethylaniline, N, N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, Tertiary amines such as quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcin, catechol; lead naphthenate, stearin Lead acid, Organic metal salts such as zinc phthalate, zinc octylate, tin oleate, dibutyltin malate, manganese naphthenate, cobalt naphthenate, and acetylacetone iron; these organic metal salts are dissolved in hydroxyl-containing compounds such as phenol and bisphenol Inorganic metal salts
  • the resin composition of the present embodiment may contain a solvent as necessary.
  • a solvent for example, when an organic solvent is used, the viscosity at the time of preparing the resin composition is lowered, the handling property is improved, and the impregnation property to the glass cloth is enhanced.
  • the kind of solvent will not be specifically limited if it can melt
  • Specific examples thereof include ketones such as acetone, methyl ethyl ketone and methyl cellosolve, aromatic hydrocarbons such as toluene and xylene, amides such as dimethylformamide, propylene glycol monomethyl ether and acetate thereof.
  • a solvent can be used individually by 1 type or in combination of 2 or more types.
  • the resin composition of the present embodiment is produced, for example, by mixing the above-described alkenyl-substituted nadiimide (A), maleimide compound (B), and amino-modified silicone (C), and other optional components as necessary. be able to.
  • a maleimide compound (B) and an amino-modified silicone (C) are polymerized to obtain a prepolymer (P), and the prepolymer (P) and an alkenyl-substituted nadiimide (A ), Maleimide compound (B), and other optional components as necessary, from the viewpoint of peel strength, desmear resistance, moldability, bleed-out of silicone components, etc. .
  • the components (A) to (C) and optional components used in the method for producing a resin composition of the present embodiment are as described in the paragraph of the resin composition.
  • an organic solvent can be used as necessary.
  • the kind of the organic solvent is not particularly limited as long as it can dissolve the resin in the resin composition. Specific examples thereof are as described above.
  • a known process for uniformly dissolving or dispersing each component can be performed.
  • the stirring and dispersing treatment is performed using a stirrer equipped with a stirrer having an appropriate stirring ability. Dispersibility is improved.
  • the above stirring, mixing, and kneading treatment can be appropriately performed using, for example, a known device such as a ball mill or a bead mill for mixing, or a revolving or rotating mixing device.
  • the prepreg of this embodiment is a prepreg obtained by impregnating or applying the above resin composition to a base material.
  • the prepreg of the present embodiment can be obtained, for example, by combining the above resin composition with a substrate, specifically, impregnating or applying the above resin composition to the substrate.
  • the manufacturing method of the prepreg of this embodiment can be performed according to a conventional method, and is not specifically limited. For example, after impregnating or coating the above-mentioned resin composition on a base material, it is semi-cured (B stage) by heating in a dryer at 100 to 200 ° C. for 1 to 30 minutes. The method of obtaining is mentioned.
  • the amount of the resin composition (including the inorganic filler) relative to the total amount of the prepreg is not particularly limited, but is preferably in the range of 30 to 90% by mass.
  • the substrate used in the prepreg of the present embodiment is not particularly limited, and known materials used for various printed wiring board materials are appropriately selected and used depending on the intended use and performance. be able to. Specific examples thereof include glass fibers such as E glass, D glass, S glass, Q glass, spherical glass, NE glass and T glass, inorganic fibers other than glass such as quartz, polyparaphenylene terephthalamide (Kevlar), and the like.
  • glass fibers such as E glass, D glass, S glass, Q glass, spherical glass, NE glass and T glass
  • inorganic fibers other than glass such as quartz, polyparaphenylene terephthalamide (Kevlar), and the like.
  • E glass cloth, T glass cloth, S glass cloth, Q glass cloth and organic fiber are preferable from the viewpoint of low thermal expansion.
  • These base materials can be used alone or in combination of two or more.
  • a shape of a base material For example, a woven fabric, a nonwoven fabric, roving, a chopped strand mat, a surfacing mat, etc. are mentioned.
  • the weaving method of the woven fabric is not particularly limited, and for example, plain weave, Nanako weave, twill weave and the like are known, and can be appropriately selected from these known ones depending on the intended use and performance. .
  • a glass woven fabric whose surface is treated with a fiber-opening treatment or a silane coupling agent is preferably used.
  • the thickness and mass of the base material are not particularly limited, but usually about 0.01 to 0.3 mm is preferably used.
  • the base material is preferably a glass woven fabric having a thickness of 200 ⁇ m or less and a mass of 250 g / m 2 or less, and a glass woven fabric made of glass fibers such as E glass, S glass, and T glass. Is more preferable.
  • the laminated board of this embodiment can be obtained by, for example, stacking and curing one or more of the above prepregs.
  • the metal foil tension laminated board of this embodiment can be obtained by laminating
  • the metal foil-clad laminate of the present embodiment can be obtained, for example, by laminating at least one or more of the prepregs described above, and arranging and molding the metal foil on one or both sides thereof.
  • a metal foil-clad laminate can be produced.
  • the metal foil used here will not be specifically limited if it is used for printed wiring board material, Well-known copper foils, such as a rolled copper foil and an electrolytic copper foil, are preferable.
  • the thickness of the metal foil is not particularly limited, but is preferably 1 to 70 ⁇ m, more preferably 1.5 to 35 ⁇ m.
  • a multi-stage press a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, etc. can be used at the time of forming a metal foil-clad laminate.
  • the temperature is generally 100 to 300 ° C.
  • the pressure is 2 to 100 kgf / cm 2
  • the heating time is generally 0.05 to 5 hours.
  • post-curing can be performed at a temperature of 150 to 300 ° C., if necessary.
  • a multilayer board can be formed by laminating and combining the above-described prepreg and a separately prepared wiring board for an inner layer.
  • the metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board by forming a predetermined wiring pattern.
  • the metal foil-clad laminate of this embodiment has a low coefficient of thermal expansion, good moldability and chemical resistance, and is particularly effective as a printed wiring board for semiconductor packages that require such performance. Can be used.
  • the present embodiment in addition to the above-described prepreg form, it may be in the form of an embedded sheet in which the above resin composition is applied to a metal foil or film.
  • the resin sheet of the present embodiment is a resin sheet obtained by applying the above-described resin composition to one side or both sides of a support.
  • the resin sheet is used as one means of thinning, and is, for example, a thermosetting resin (including an inorganic filler) directly used for a prepreg or the like on a support such as a metal foil or a film. Can be applied and dried.
  • the support used in producing the resin sheet of the present embodiment is not particularly limited, and known materials used for various printed wiring board materials can be used. Examples thereof include a polyimide film, a polyamide film, a polyester film, a polyethylene terephthalate (PET) film, a polybutylene terephthalate (PBT) film, a polypropylene (PP) film, a polyethylene (PE) film, an aluminum foil, a copper foil, and a gold foil. Among these, electrolytic copper foil and PET film are preferable.
  • the resin sheet of the present embodiment is particularly preferably one obtained by applying the above-described resin composition to a support and then semi-curing (B-stage).
  • the method for producing the resin sheet of this embodiment is preferably a method for producing a composite of a B-stage resin and a support.
  • the resin composition is coated on a support such as a copper foil, and then semi-cured by a method of heating in a dryer at 100 to 200 ° C. for 1 to 60 minutes to produce a resin sheet. The method of doing is mentioned.
  • the amount of the resin composition attached to the support is preferably in the range of 1 to 300 ⁇ m in terms of the resin thickness of the resin sheet.
  • the resin sheet of this embodiment can be used as a build-up material for printed wiring boards.
  • the laminated board of this embodiment can be obtained, for example, by stacking and curing one or more of the above-described resin sheets.
  • the metal foil tension laminated board of this embodiment can be obtained by laminating
  • the metal foil-clad laminate of the present embodiment can be obtained by, for example, using the above-mentioned resin sheet and arranging and laminating metal foils on one side or both sides thereof. More specifically, for example, a single resin sheet as described above or a plurality of sheets from which the support is peeled off as desired are stacked, and a metal foil such as copper or aluminum is disposed on one or both sides thereof.
  • a metal foil-clad laminate can be produced by laminating as necessary.
  • the metal foil used here will not be specifically limited if it is used for printed wiring board material, Well-known copper foils, such as a rolled copper foil and an electrolytic copper foil, are preferable.
  • the method for forming the metal foil-clad laminate and the molding conditions thereof There are no particular limitations on the method for forming the metal foil-clad laminate and the molding conditions thereof, and general methods and conditions for a laminate for a printed wiring board and a multilayer board can be applied.
  • a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, etc. can be used at the time of forming a metal foil-clad laminate.
  • the temperature is generally 100 to 300 ° C.
  • the pressure is 2 to 100 kgf / cm 2
  • the heating time is generally 0.05 to 5 hours.
  • post-curing can be performed at a temperature of 150 to 300 ° C., if necessary.
  • the laminate of this embodiment may be a laminate obtained by laminating and curing one or more resin sheets and prepregs each, and is obtained by laminating and curing a resin sheet, prepreg, and metal foil. It may be a metal foil-clad laminate.
  • the printed wiring board of this embodiment is a printed wiring board including an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer includes the resin composition described above.
  • the printed wiring board according to the present embodiment is produced, for example, by forming a conductive layer serving as a circuit on an insulating layer by metal foil or electroless plating.
  • the conductor layer is generally made of copper or aluminum.
  • the insulating layer for printed wiring board on which the conductor layer is formed can be suitably used for a printed wiring board by forming a predetermined wiring pattern.
  • the printed wiring board of this embodiment maintains the elastic modulus excellent also under the reflow temperature at the time of semiconductor mounting because an insulating layer contains the above-mentioned resin composition, and effectively warps a semiconductor plastic package. Therefore, it can be used particularly effectively as a printed wiring board for semiconductor packages.
  • the printed wiring board of the present embodiment can be manufactured by the following method, for example.
  • the metal foil-clad laminate such as a copper-clad laminate
  • An inner layer circuit is formed by etching the surface of the metal foil-clad laminate to produce an inner layer substrate. If necessary, surface treatment is performed on the inner layer circuit surface of the inner layer substrate to increase the adhesive strength, then the required number of the prepregs are stacked on the inner layer circuit surface, and a metal foil for the outer layer circuit is laminated on the outer side. Then, it is integrally molded by heating and pressing.
  • a multilayer laminate is produced in which an insulating layer made of a cured material of the base material and the thermosetting resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit.
  • desmear treatment is performed to remove smears, which are resin residues derived from the resin component contained in the cured product layer.
  • a plated metal film is formed on the wall surface of this hole to connect the inner layer circuit and the metal foil for the outer layer circuit, and the outer layer circuit is formed by etching the metal foil for the outer layer circuit to produce a printed wiring board. Is done.
  • the above-described prepreg base material and the above-described resin composition attached thereto
  • the above-described resin sheet the support and the above-described resin composition attached thereto
  • the resin composition layer of the metal foil-clad laminate constitutes an insulating layer containing the above-described resin composition.
  • the insulating layer preferably has a difference between the bending elastic modulus at 25 ° C. and the bending elastic modulus at 250 ° C. of 20% or less, more preferably 0 to 20%. Preferably, it is 0 to 15%.
  • the insulating layer has a good elastic modulus maintenance rate.
  • the elastic modulus maintenance factor refers to the ratio of the flexural modulus at 250 ° C. to the flexural modulus at 25 ° C.
  • the method for setting the difference between the bending elastic modulus at 25 ° C. and the bending elastic modulus at 250 ° C. within 20% of the insulating layer is not particularly limited, but for example, a resin used for the insulating layer A method of appropriately adjusting the type and content of each component of the composition to the above-described range is exemplified.
  • Example 1 30 parts by mass of maleimide compound (BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.) and diamino-modified silicone (X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.) (Manufactured) 15 parts by mass was polymerized to obtain a prepolymer.
  • maleimide compound BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.
  • diamino-modified silicone X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.
  • the obtained prepolymer 25 parts by mass of bisdiallylnadiimide (BANI-M, alkenyl group equivalent 286 g / eq, manufactured by Maruzen Petrochemical Co., Ltd.), maleimide compound (BMI-2300, maleimide group equivalent 186 g / eq, Daiwa Kasei Co., Ltd.) Kogyo Co., Ltd.) 30 parts by mass, epoxy silane coupling agent (Z6040, Toray Dow Coating Co., Ltd.) 5 parts by mass, wetting and dispersing agent (DISPERBYK-161, manufactured by Big Chemie Japan) 1 part by mass , 0.5 parts by mass of a wetting and dispersing agent (DISPERBYK-111, manufactured by Big Chemie Japan Co., Ltd.), 120 parts by mass of slurry silica (SC-2050MB, manufactured by Admatex Co., Ltd.), and 2,4,5-triphenyl 0.5 parts by mass of imidazole (TPIZ, manufactured by Wak
  • the number of maleimide groups / the number of amino groups and the number of alkenyl groups / the number of maleimide groups are represented by the following formulas.
  • Numberer of maleimide groups / number of amino groups] (mass parts of maleimide compound / maleimide group equivalent of maleimide compound) / (mass part of diamino modified silicone / amino group equivalent of diamino modified silicone)
  • Numberer of alkenyl groups / number of maleimide groups] (mass parts of bisdiallylnadiimide / alkenyl group equivalents of bisdiallylnadiimide) / (mass parts of maleimide compounds / maleimide group equivalents of maleimide compounds)
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg
  • Example 2 15 parts by mass of maleimide compound (BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.) and diamino-modified silicone (X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.) (Manufactured) 10 parts by mass was polymerized to obtain a prepolymer.
  • maleimide compound BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.
  • diamino-modified silicone X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.
  • the resulting prepolymer 30 parts by mass of bisdiallylnadiimide (BANI-M, alkenyl group equivalent 286 g / eq, manufactured by Maruzen Petrochemical Co., Ltd.), maleimide compound (BMI-2300, maleimide group equivalent 186 g / eq, Daiwa Kasei Co., Ltd.) 35 parts by mass of Kogyo Co., Ltd., 5 parts by mass of epoxy silane coupling agent (Z6040, manufactured by Toray Dow Coating Co., Ltd.), 120 parts by mass of slurry silica (SC-2050MB, manufactured by Admatex Co., Ltd.), biphenyl Aralkyl type epoxy resin (NC3000FH, manufactured by Nippon Kayaku Co., Ltd.) 9.5 parts by mass, 2,2-bis (4-cyanatephenyl) propane prepolymer (CA210, manufactured by Mitsubishi Gas Chemical) 0.5 parts by mass and 0.5 part by mass of 2,4,5-triphenylimidazole (
  • a varnish was obtained by diluting the obtained resin composition having a maleimide group number / amino group number ratio of 7.9 and an alkenyl group number / maleimide group number of 2.3 with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 44.5% by mass.
  • Example 3 25 parts by mass of maleimide compound (BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.) and diamino modified silicone (X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.) (Manufactured) 15 parts by mass was polymerized to obtain a prepolymer.
  • maleimide compound BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.
  • diamino modified silicone X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.
  • the obtained prepolymer 25 parts by mass of bisdiallylnadiimide (BANI-M, alkenyl group equivalent 286 g / eq, manufactured by Maruzen Petrochemical Co., Ltd.), maleimide compound (BMI-2300, maleimide group equivalent 186 g / eq, Daiwa Kasei Co., Ltd.) Kogyo Co., Ltd.) 30 parts by mass, epoxy silane coupling agent (Z6040, Toray Dow Coating Co., Ltd.) 5 parts by mass, wetting and dispersing agent (DISPERBYK-161, manufactured by Big Chemie Japan) 1 part by mass , 0.5 parts by weight of a wetting and dispersing agent (DISPERBYK-111, manufactured by Big Chemie Japan Co., Ltd.), 120 parts by weight of slurry silica (SC-2050MB, manufactured by Admatex Co., Ltd.), biphenyl aralkyl type epoxy resin (NC3000FH, Japan) 4.5 parts by mass
  • Nyl propane prepolymer (CA210, manufactured by Mitsubishi Gas Chemical Co., Ltd.) 0.5 parts by mass was obtained to obtain a resin composition having a maleimide group number / amino group number ratio of 8.8 and an alkenyl group number / maleimide group number of 2.8. .
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 44.5% by mass.
  • Example 4 25 parts by mass of maleimide compound (BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.) and diamino modified silicone (X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.) (Manufactured) 15 parts by mass was polymerized to obtain a prepolymer.
  • maleimide compound BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.
  • diamino modified silicone X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.
  • a resin composition having an alkenyl group number / maleimide group number of 2.8 was obtained.
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and applied to a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 47.0% by mass.
  • Example 5 25 parts by mass of maleimide compound (BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.) and diamino modified silicone (X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.) (Manufactured) 15 parts by mass was polymerized to obtain a prepolymer.
  • maleimide compound BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.
  • diamino modified silicone X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and applied to a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 47.0% by mass.
  • Example 6 25 parts by mass of maleimide compound (BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.) and diamino modified silicone (X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.) (Manufactured) 15 parts by mass was polymerized to obtain a prepolymer.
  • maleimide compound BMI-80, maleimide group equivalent 285 g / eq, manufactured by Kay Kasei Co., Ltd.
  • diamino modified silicone X-22-161B, amino group equivalent 1500 g / eq, Shin-Etsu Chemical Co., Ltd.
  • a resin composition having a maleimide group number of 2.8 was obtained.
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 43.0% by mass.
  • BANI-M bisdiallyln
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 44.5% by mass.
  • maleimide compound (BMI-70, maleimide group equivalent 221 g / eq, manufactured by Kay Kasei Co., Ltd.) 10 parts by mass, maleimide compound (BMI-2300, maleimide group equivalent 186 g / eq, Daiwa Kasei Kogyo) 5 parts by mass of epoxy silane coupling agent (Z6040, manufactured by Toray Dow Coating Co., Ltd.), 3 parts by mass of wetting and dispersing agent (DISPERBYK-161, manufactured by Big Chemie Japan Co., Ltd.), 10 parts by mass of silicon resin powder (Tospearl, manufactured by Momentive Performance Materials Japan GK), 120 parts by mass of slurry silica (SC-2050MB, manufactured by Admatex), biphenyl aralkyl type epoxy resin (NC3000FH, Nipponized) 30 parts by mass of Yakuhin Co., Ltd.
  • epoxy silane coupling agent Z6040, manufactured by Toray Dow Coating Co., Ltd.
  • Example resultant ⁇ - naphthol aralkyl type cyanate ester resin 40 parts by mass were mixed with 1 to obtain a resin composition.
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 44.5% by mass.
  • a varnish was obtained by diluting the obtained resin composition with methyl ethyl ketone. This varnish was impregnated and coated on a 0.1 mm S glass woven fabric and dried by heating at 160 ° C. for 3 minutes to obtain a prepreg having a resin composition content of 44.5% by mass.
  • Table 1 shows the results of measuring the flexural modulus, thermal expansion coefficient, and solder heat resistance using the obtained copper-clad laminate.
  • Bending elastic modulus Using a sample of 50 mm ⁇ 25 mm ⁇ 0.8 mm, measurement was carried out at 25 ° C. and 250 ° C. respectively with an autograph (AG-Xplus manufactured by Shimadzu Corporation) according to JIS standard C6481. .
  • Elastic modulus maintenance factor Calculated by the following formula from the bending elastic modulus (a) at 25 ° C. and the hot bending elastic modulus (b) at 250 ° C. measured by the above method.
  • Coefficient of thermal expansion Using a sample of 4.5 mm ⁇ 30 mm ⁇ 0.1 mm, the temperature was increased from 40 ° C. to 340 ° C. at 10 ° C. per minute with a thermomechanical analyzer (TA Instruments), and from 60 ° C. to 120 ° C. The linear expansion coefficient in the plane direction at ° C was measured. The measurement direction was the longitudinal direction (Warp) of the glass cloth of the laminate.
  • Evaluation of heat resistance was performed by the following method using a copper foil-clad laminate. Heat resistance: A 50 ⁇ 50 mm sample was floated on 288 ° C. solder for 30 minutes, and the time until delamination occurred was measured. When delamination did not occur even after 30 minutes, it was expressed as> 30 min in the table.
  • the resin composition of the present invention and a printed wiring board containing the resin composition can be suitably used as members of various electronic devices such as personal computers and communication devices.

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Abstract

La composition de résine de l'invention contient un nadimide à alcényle substitué (A), un composé maléimide (B) et une silicone amino-modifiée (C).
PCT/JP2016/069739 2015-07-06 2016-07-04 Composition de résine, pré-imprégné ou feuille de résine mettant en œuvre cette composition, plaque stratifiée mettant en œuvre ceux-ci, et carte de circuit imprimé Ceased WO2017006888A1 (fr)

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JP2017527438A JP6774032B2 (ja) 2015-07-06 2016-07-04 樹脂組成物、該樹脂組成物を用いたプリプレグ又はレジンシート並びにそれらを用いた積層板及びプリント配線板
US15/738,400 US10703874B2 (en) 2015-07-06 2016-07-04 Resin composition, prepreg or resin sheet comprising the resin composition, and laminate and printed circuit board comprising them
EP16821357.7A EP3321289B1 (fr) 2015-07-06 2016-07-04 Composition de resine, prepreg ou feuille de resine comprenant la composition de resine, et stratifie et carte de circuit imprime les comprenant
KR1020177033056A KR102605760B1 (ko) 2015-07-06 2016-07-04 수지 조성물, 그 수지 조성물을 사용한 프리프레그 또는 레진 시트 그리고 그것들을 사용한 적층판 및 프린트 배선판
CN201680039769.1A CN107735409B (zh) 2015-07-06 2016-07-04 树脂组合物、使用该树脂组合物的预浸料或树脂片以及使用它们的层叠板和印刷电路板

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JPWO2021192680A1 (fr) * 2020-03-25 2021-09-30
JPWO2023243676A1 (fr) * 2022-06-17 2023-12-21
WO2025053233A1 (fr) * 2023-09-07 2025-03-13 株式会社レゾナック Composition de résine thermodurcissable, préimprégné, film de résine, stratifié, carte de circuit imprimé et boîtier de semi-conducteur

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JP6934638B2 (ja) * 2017-12-21 2021-09-15 パナソニックＩｐマネジメント株式会社 半導体パッケージ及びプリント回路板
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JP2018131590A (ja) * 2017-02-17 2018-08-23 日立化成株式会社 コアレス基板用熱硬化性樹脂組成物、コアレス基板用プリプレグ、コアレス基板、コアレス基板の製造方法及び半導体パッケージ
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WO2021192680A1 (fr) * 2020-03-25 2021-09-30 三菱瓦斯化学株式会社 Composition de résine, préimprégné, feuille de résine, carte stratifiée, carte stratifiée plaquée de feuille métallique et carte de circuit imprimé
JP7799974B2 (ja) 2020-03-25 2026-01-16 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、樹脂シート、積層板、金属箔張積層板、及びプリント配線板
JPWO2023243676A1 (fr) * 2022-06-17 2023-12-21
WO2023243676A1 (fr) * 2022-06-17 2023-12-21 株式会社レゾナック Composition de résine, préimprégné, stratifié, film de résine, carte de circuit imprimé et boîtier de semi-conducteur
JP7517620B2 (ja) 2022-06-17 2024-07-17 株式会社レゾナック 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ
WO2025053233A1 (fr) * 2023-09-07 2025-03-13 株式会社レゾナック Composition de résine thermodurcissable, préimprégné, film de résine, stratifié, carte de circuit imprimé et boîtier de semi-conducteur

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KR102605760B1 (ko) 2023-11-23
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CN107735409B (zh) 2020-08-11
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EP3321289A1 (fr) 2018-05-16
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